アミドとアジドの化学的およびステレオ選択的移行金属無アミネーション

Veronica Tona¹, Aurélien de la Torre¹, Mohan Padmanaban¹

¹Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna , Währinger Strasse 38, 1090 Vienna, Austria.

Journal of the American Chemical Society

|June 29, 2016

まとめ

この研究では,単純なアジドとアミドを使用してアルファアミノカルボニル化合物を生成する新しい方法が紹介されています. このステレオ選択反応は効率的で軽いもので,光学的に豊かな製品を生成します.

科学分野:

有機合成
ステレオ選択合成

背景:

アルファアミノカルボニルおよびカルボキシル化合物の合成は,現代の有機化学における重要な課題である.
これらの貴重な構成要素にアクセスするための効率的でステレオ選択的な方法の開発は,様々な用途において極めて重要です.

研究の目的:

単純なアジドを用いたアミドの新型ステレオセレクティブアルファ-アミネーションを提示する.
アルファアミノカルボニル/カルボキシル化合物の温和で効率的な合成経路を確立する.
開発されたアミネーション方法の化学選択性と多用途性を実証する.

主な方法:

単純なアジドをアミドのアミナ化剤として使用する.
反応の制限反応剤としてアミドを使用する.
アルファ-アミネーションプロセスのステレオ選択性と化学選択性の調査.
アジド成分の多様性を探求し,様々な代替製品を得ること.

主要な成果:

軽度の反応条件下でアミドのステレオ選択的アルファ-アミネーションを達成した.
副産物として窒素ガスの放出が観察された.
エステルやケトンの存在でも,アミドに対する高い化学選択性を示した.
光学的に濃縮されたアルファアミノカルボニル/カルボキシル化合物を成功裏に製造した.

結論:

開発された方法は,アルファアミノカルボニル/カルボキシル化合物への容易でステレオ選択的な経路を提供します.
反応の温和な条件,高い化学選択性,そして光学的に濃縮された製品を生成する能力は,有機合成において貴重なツールとなる.
アジドパターンの単純な変異は,広範囲の置換アミナ化製品の合成を可能にします.

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